Everyone has a first time. When you first start considering investment, the initial questions are usually:
“What valuation can we get?”
“How much dilution will there be?”
And before you know it, you’re thinking, “These terms don’t seem too bad.”

Especially when your runway is running short, the urgency becomes overwhelming.
“If we just secure this funding now, we can keep the team and finish building the product.”

But the real problem comes after the money lands.
Even if you breathe a little easier for now,
a misalignment in your investor’s style or a lack of understanding about your business
can turn into major obstacles in your next round.

In this article, I want to share five things every founder should check before taking their first investment—based on my own experiences.
Personal opinions are included.

Can they support your next round?

You must ensure that your seed investor can help you transition smoothly into the next round.
Once the contract is signed and the money hits your account, time moves fast.
You’ll be working hard to hit your KPIs, and if you’re left to find Series A investors alone, it’s a huge drain on time and energy.

In most cases, investors have broader networks and more up-to-date intel on the funding landscape than you do.
So, helping with the next round isn’t a bonus—it’s a basic responsibility.
If that support is missing, all the pressure falls back on you, and your odds of success shrink.

Of course, founders should still make efforts to build investor relationships and deliver strong traction.
But as we all know, the most effective connections usually come through warm intros.

Checkpoints

• Can this investor introduce you to Series A or growth-stage VCs?
• Have their past portfolio companies successfully raised follow-ons?
• Do they have experience with bridge or follow-on investments themselves?
• Are they already discussing exit scenarios or next-round strategies with you?

Personally, I believe this is the single most important factor in early-stage fundraising.

Can they help fill in your blind spots?

In some overseas markets, it’s not uncommon to see teams raise a Series A within 3–6 months of their seed round.
Is that because the startup was just that good?
Not necessarily.
It’s often thanks to hands-on support from investors—former operators who truly understand growth.

These investors don’t just write a check.
They help build the business—offering advice on GTM strategy, channel partnerships, even joining customer interviews.

To many Korean founders, this might sound almost too ideal.
And it’s true that we don’t have many domain-specific ACs and VCs yet in Korea.
Most investors come from finance, consulting, or accounting backgrounds,
and their broad investment scope makes deep strategic advice difficult.

That said, things are changing.
As founders continue to raise their expectations and global ACs and VCs enter the Korean market,
we’re now seeing more investors who actively contribute beyond the check.

Checkpoints

• Can this investor give you real, practical feedback in your weak areas?
• Can they introduce you to external partners, customers, or channels?
• Have they contributed meaningful support to other portfolio companies?

Check their reputation and talk to founders directly

Post-investment, the relationship is no longer about contracts—it’s about people.
How your investor communicates, operates, and manages expectations can have a huge impact on your business.

I know a startup that, immediately after raising its seed round, was asked to submit quarterly financials and monthly operating reports.
But none of this reporting was tied to actual strategic advice or support—it became a time sink that drained their ability to execute.

Sure, for later-stage companies, reporting structures are necessary.
But for an early-stage startup, unrealistic demands can get in the way of progress.

Checkpoints

• How does this investor work with founders after the deal?
• Are their requests aligned with what actually helps the business?
• What do their existing portfolio founders say about them?

Review their portfolio

Sometimes, an investor shows strong interest in your company even though they’ve never invested in your space.
Maybe they want to enter a new sector, or maybe they’re just personally curious.

That’s not necessarily a red flag—until the deal closes.

If they lack real domain knowledge, they’ll likely give feedback based on surface-level metrics.
You may find that they can’t have strategic conversations,
and the advice you get feels like textbook generalities, not grounded support.

Checkpoints

• What industries or product types has this VC invested in?
• Where are those portfolio companies now?
• Can you speak to one of the founders they’ve backed in a similar space?

Do they truly understand your vision?

This one’s especially important for deep tech or category-creating startups.
If your investor doesn’t share your vision—or worse, constantly pushes you toward quick wins and pivots—it can shake your foundation.

When the market is still forming and customer feedback is limited, pressure for short-term results can force repeated pivots.
The more they interfere with product direction, customer targeting, or sales strategy,
the more you lose strategic clarity—and waste resources.

This isn’t about bad intentions—it’s often just a mismatch in direction.
But even so, that mismatch can cost you time, energy, and momentum.
And when time is your most valuable asset, it’s a serious risk.

Checkpoints

• Do they truly understand the problem you’re solving?
• Have they asked thoughtful, detailed questions about your strategy?
• Are they more interested in your unique approach, or just following the hype?

Work with someone who believes in you.
Even a big check isn’t worth it if you’re pulling in different directions.
You may end up losing more energy than money.

Final Thoughts

The most important question in your first raise isn’t valuation.
It’s:
“Do I genuinely want to work with this person?”

The reality is—it’s hard to find that kind of partner.
And when your runway is short, urgency often wins out.

Still, I hope this post helps more founders find the right investor at the right time.
And on the flip side, that investors also find founders who are truly aligned.

Thanks for reading.